6-acetyl-2-(cyclopropanecarboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide | 848331-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 6-acetyl-2-(cyclopropanecarboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide
• 英文别名: 6-acetyl-2-(cyclopropanecarbonylamino)-5,7-dihydro-4H-thieno[2,3-c]pyridine-3-carboxamide
• CAS: 848331-83-9
• 化学式: C₁₄H₁₇N₃O₃S
• 分子量: 307.373
• InChiKey: ZQMQNMBAKOFIIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  569.3±50.0 °C(Predicted)
• 密度：
  1.469±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-3-氨基甲酰-4,7-二氢-5H-噻吩并[2,3-c]吡啶-6-羧酸叔丁酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 6-acetyl-2-(cyclopropanecarboxamido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide
  参考文献：
  名称：

  Development of antimycobacterial tetrahydrothieno[2,3-c]pyridine-3-carboxamides and hexahydrocycloocta[b]thiophene-3-carboxamides: Molecular modification from known antimycobacterial lead

  摘要：

  Twenty derivatives of 2,6-disubstituted 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide and ten of 2-substituted 4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxamide were synthesized by molecular modification of a known antimycobacterial molecule. Compounds were evaluated in vitro against Mycobacterium tuberculosis (MTB), and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-(4-phenoxybenzamido)-4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxamide (12f) was found to be the most active compound against MTB with MIC of 3.70 mu M and was more potent than Ethambutol (MIC of 7.64 mu M), Ciprofloxacin (MIC of 9.41 mu M) and standard lead compound SID 92097880 (MIC of 9.15 mu M). Compound 12f also showed MTB MIC of 1.23 mu M in the presence of an efflux pump inhibitor verapamil, and showed no cytotoxicity at 50 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.028

文献信息

• Heterobicyclic Compounds as Pharmaceutically Active Agents
  申请人：Koul Anil

  公开号：US20070275962A1

  公开（公告）日：2007-11-29

  Described are heterobicyclic compounds such as 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]thiopyran 3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid amides, or benzo[b]thiophene-3-carboxylic acid amides and pharmaceutically acceptable salts thereof, the use of these derivatives for the prophylaxis and/or treatment of various diseases such as infectious diseases, including mycobacteriainduced infections and opportunistic diseases, prion diseases, immunological diseases, autoimmune diseases, bipolar and clinical disorders, cardiovascular diseases, cell proliferative diseases, diabetes, inflammation, transplant rejections, erectile dysfunction, neurodegenerative diseases and stroke, as well as compositions containing at least one heterobicyclic compound and/or pharmaceutically acceptable salts thereof. Furthermore, reaction procedures for the synthesis of the heterobicyclic compound are disclosed.

  本文介绍了异杂双环化合物，例如4,5,6,7-四氢苯并[b]噻吩-3-羧酸酰胺，4,7-二氢-5H-噻吩[2,3-c]硫杂吡喃-3-羧酸酰胺，4,7-二氢-5H-噻吩[2,3-c]吡喃-3-羧酸酰胺，或苯并[b]噻吩-3-羧酸酰胺及其药学上可接受的盐。这些衍生物的用途包括预防和/或治疗各种疾病，如传染性疾病，包括分支杆菌感染和机会性疾病，朊病，免疫性疾病，自身免疫性疾病，双相和临床障碍，心血管疾病，细胞增殖性疾病，糖尿病，炎症，移植排斥，勃起功能障碍，神经退行性疾病和中风，以及含有至少一种异杂双环化合物和/或药学上可接受的盐的组合物。此外，还公开了合成异杂双环化合物的反应程序。
• HETEROBICYCLIC COMPOUNDS AS PHARMACEUTICALLY ACTIVE AGENTS
  申请人：GPC Biotech AG

  公开号：EP1670804A2

  公开（公告）日：2006-06-21
• [EN] HETEROBICYCLIC COMPOUNDS AS PHARMACEUTICALLY ACTIVE AGENTS<br/>[FR] COMPOSES HETEROBICYCLIQUES EN TANT QU'AGENTS ACTIFS AU NIVEAU PHARMACEUTIQUE
  申请人：AXXIMA PHARMACEUTICALS AG

  公开号：WO2005023818A2

  公开（公告）日：2005-03-17

  Described are heterobicyclic compounds such as 4,5,6,7-tetrahydro­benzo[b]thiophene-3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]thiopyran­ 3-carboxylic acid amides, 4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid amides, or benzo[b]thiophene-3-carboxylic acid amides and pharmaceutically acceptable salts thereof, the use of these derivatives for the prophylaxis and/or treatment of various diseases such as infectious diseases, including mycobacteria­induced infections and opportunistic diseases, prion diseases, immunological diseases, autoimmune diseases, bipolar and clinical disorders, cardiovascular diseases, cell proliferative diseases, diabetes, inflammation, transplant rejections, erectile dysfunction, neurodegenerative diseases and stroke, as well as compositions containing at least one heterobicyclic compound and/or pharmaceutically acceptable salts thereof. Furthermore, reaction procedures for the synthesis of the heterobicyclic compound are disclosed.
• Development of antimycobacterial tetrahydrothieno[2,3-c]pyridine-3-carboxamides and hexahydrocycloocta[b]thiophene-3-carboxamides: Molecular modification from known antimycobacterial lead
  作者：Radhika Nallangi、Ganesh Samala、Jonnalagadda Padma Sridevi、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2014.02.028

  日期：2014.4

  Twenty derivatives of 2,6-disubstituted 4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide and ten of 2-substituted 4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxamide were synthesized by molecular modification of a known antimycobacterial molecule. Compounds were evaluated in vitro against Mycobacterium tuberculosis (MTB), and cytotoxicity against RAW 264.7 cell line. Among the compounds, 2-(4-phenoxybenzamido)-4,5,6,7,8,9-hexahydrocycloocta[b]thiophene-3-carboxamide (12f) was found to be the most active compound against MTB with MIC of 3.70 mu M and was more potent than Ethambutol (MIC of 7.64 mu M), Ciprofloxacin (MIC of 9.41 mu M) and standard lead compound SID 92097880 (MIC of 9.15 mu M). Compound 12f also showed MTB MIC of 1.23 mu M in the presence of an efflux pump inhibitor verapamil, and showed no cytotoxicity at 50 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.